ES2247617T3 - Procesos para recuperar las isoflavonas de las mezclas de soja. - Google Patents

Procesos para recuperar las isoflavonas de las mezclas de soja.

Info

Publication number: ES2247617T3
Authority: ES; Spain
Prior art keywords: isoflavone; enriched; soy molasses; isoflavones; soy
Prior art date: 1996-06-11
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired - Lifetime

Application number

ES97304076T

Other languages

English (en)

Spanish (es)

Inventor

Doyle H. Waggle

Barbara A. Bryan

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Archer Daniels Midland Co

Original Assignee

Archer Daniels Midland Co

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1996-06-11

Filing date

1997-06-11

Publication date

2006-03-01

1997-06-11 Application filed by Archer Daniels Midland Co filed Critical Archer Daniels Midland Co

2006-03-01 Application granted granted Critical

2006-03-01 Publication of ES2247617T3 publication Critical patent/ES2247617T3/es

2017-06-11 Anticipated expiration legal-status Critical

Status Expired - Lifetime legal-status Critical Current

Links

CJWQYWQDLBZGPD-UHFFFAOYSA-N isoflavone Natural products C1=C(OC)C(OC)=CC(OC)=C1C1=COC2=C(C=CC(C)(C)O3)C3=C(OC)C=C2C1=O CJWQYWQDLBZGPD-UHFFFAOYSA-N 0.000 title claims abstract description 343
235000008696 isoflavones Nutrition 0.000 title claims abstract description 343
150000002515 isoflavone derivatives Chemical class 0.000 title claims abstract description 96
238000000034 method Methods 0.000 title claims abstract description 53
230000008569 process Effects 0.000 title claims description 36
239000000203 mixture Substances 0.000 title claims description 8
GOMNOOKGLZYEJT-UHFFFAOYSA-N isoflavone Chemical compound C=1OC2=CC=CC=C2C(=O)C=1C1=CC=CC=C1 GOMNOOKGLZYEJT-UHFFFAOYSA-N 0.000 claims abstract description 201
235000013379 molasses Nutrition 0.000 claims abstract description 184
239000000463 material Substances 0.000 claims abstract description 179
229930182470 glycoside Natural products 0.000 claims description 107
102000004190 Enzymes Human genes 0.000 claims description 62
108090000790 Enzymes Proteins 0.000 claims description 61
150000002338 glycosides Chemical class 0.000 claims description 55
-1 isoflavone glycosides Chemical class 0.000 claims description 54
239000000725 suspension Substances 0.000 claims description 32
239000007787 solid Substances 0.000 claims description 23
230000000295 complement effect Effects 0.000 claims description 17
238000001914 filtration Methods 0.000 claims description 7
238000005119 centrifugation Methods 0.000 claims description 5
239000007900 aqueous suspension Substances 0.000 claims description 4
238000006243 chemical reaction Methods 0.000 abstract description 58
238000011084 recovery Methods 0.000 abstract description 7
229930182478 glucoside Natural products 0.000 abstract description 2
150000008131 glucosides Chemical class 0.000 abstract description 2
235000010469 Glycine max Nutrition 0.000 description 187
229940088598 enzyme Drugs 0.000 description 56
ZQSIJRDFPHDXIC-UHFFFAOYSA-N daidzein Chemical compound C1=CC(O)=CC=C1C1=COC2=CC(O)=CC=C2C1=O ZQSIJRDFPHDXIC-UHFFFAOYSA-N 0.000 description 32
ZCOLJUOHXJRHDI-CMWLGVBASA-N genistein 7-O-beta-D-glucoside Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1OC1=CC(O)=C2C(=O)C(C=3C=CC(O)=CC=3)=COC2=C1 ZCOLJUOHXJRHDI-CMWLGVBASA-N 0.000 description 30
ZWSNUPOSLDAWJS-QNDFHXLGSA-N 6,7-dihydroxy-3-[4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]chromen-4-one Chemical compound OC[C@H]1O[C@@H](Oc2ccc(cc2)-c2coc3cc(O)c(O)cc3c2=O)[C@H](O)[C@@H](O)[C@@H]1O ZWSNUPOSLDAWJS-QNDFHXLGSA-N 0.000 description 26
238000010790 dilution Methods 0.000 description 26
239000012895 dilution Substances 0.000 description 26
235000006539 genistein Nutrition 0.000 description 25
TZBJGXHYKVUXJN-UHFFFAOYSA-N genistein Natural products C1=CC(O)=CC=C1C1=COC2=CC(O)=CC(O)=C2C1=O TZBJGXHYKVUXJN-UHFFFAOYSA-N 0.000 description 25
229940045109 genistein Drugs 0.000 description 25
244000068988 Glycine max Species 0.000 description 24
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 20
235000007240 daidzein Nutrition 0.000 description 16
238000000926 separation method Methods 0.000 description 16
210000002966 serum Anatomy 0.000 description 15
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
108010005774 beta-Galactosidase Proteins 0.000 description 11
239000007788 liquid Substances 0.000 description 11
102100026189 Beta-galactosidase Human genes 0.000 description 10
ZCOLJUOHXJRHDI-FZHKGVQDSA-N Genistein 7-O-glucoside Natural products O([C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@H](CO)O1)c1cc(O)c2C(=O)C(c3ccc(O)cc3)=COc2c1 ZCOLJUOHXJRHDI-FZHKGVQDSA-N 0.000 description 10
CJPNHKPXZYYCME-UHFFFAOYSA-N Genistin Natural products OCC1OC(Oc2ccc(O)c3OC(=CC(=O)c23)c4ccc(O)cc4)C(O)C(O)C1O CJPNHKPXZYYCME-UHFFFAOYSA-N 0.000 description 10
108010059881 Lactase Proteins 0.000 description 10
YCUNGEJJOMKCGZ-UHFFFAOYSA-N Pallidiflorin Natural products C1=CC(OC)=CC=C1C1=COC2=CC=CC(O)=C2C1=O YCUNGEJJOMKCGZ-UHFFFAOYSA-N 0.000 description 10
229940116108 lactase Drugs 0.000 description 10
239000007858 starting material Substances 0.000 description 10
235000008466 glycitein Nutrition 0.000 description 9
NNUVCMKMNCKPKN-UHFFFAOYSA-N glycitein Natural products COc1c(O)ccc2OC=C(C(=O)c12)c3ccc(O)cc3 NNUVCMKMNCKPKN-UHFFFAOYSA-N 0.000 description 9
DXYUAIFZCFRPTH-UHFFFAOYSA-N glycitein Chemical compound C1=C(O)C(OC)=CC(C2=O)=C1OC=C2C1=CC=C(O)C=C1 DXYUAIFZCFRPTH-UHFFFAOYSA-N 0.000 description 9
239000000047 product Substances 0.000 description 9
239000002253 acid Substances 0.000 description 8
101000718529 Saccharolobus solfataricus (strain ATCC 35092 / DSM 1617 / JCM 11322 / P2) Alpha-galactosidase Proteins 0.000 description 7
NNISLDGFPWIBDF-MPRBLYSKSA-N alpha-D-Gal-(1->3)-beta-D-Gal-(1->4)-D-GlcNAc Chemical compound O[C@@H]1[C@@H](NC(=O)C)C(O)O[C@H](CO)[C@H]1O[C@H]1[C@H](O)[C@@H](O[C@@H]2[C@@H]([C@@H](O)[C@@H](O)[C@@H](CO)O2)O)[C@@H](O)[C@@H](CO)O1 NNISLDGFPWIBDF-MPRBLYSKSA-N 0.000 description 7
238000009826 distribution Methods 0.000 description 7
230000000694 effects Effects 0.000 description 7
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 6
230000002378 acidificating effect Effects 0.000 description 6
239000003153 chemical reaction reagent Substances 0.000 description 6
150000001875 compounds Chemical class 0.000 description 6
239000000284 extract Substances 0.000 description 6
239000008103 glucose Substances 0.000 description 6
239000012141 concentrate Substances 0.000 description 5
235000018102 proteins Nutrition 0.000 description 5
108090000623 proteins and genes Proteins 0.000 description 5
102000004169 proteins and genes Human genes 0.000 description 5
206010006187 Breast cancer Diseases 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
WUADCCWRTIWANL-UHFFFAOYSA-N biochanin A Chemical compound C1=CC(OC)=CC=C1C1=COC2=CC(O)=CC(O)=C2C1=O WUADCCWRTIWANL-UHFFFAOYSA-N 0.000 description 4
238000002474 experimental method Methods 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 3
208000026310 Breast neoplasm Diseases 0.000 description 3
108010073178 Glucan 1,4-alpha-Glucosidase Proteins 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
102000007544 Whey Proteins Human genes 0.000 description 3
108010046377 Whey Proteins Proteins 0.000 description 3
230000007423 decrease Effects 0.000 description 3
150000002148 esters Chemical class 0.000 description 3
238000000605 extraction Methods 0.000 description 3
238000004519 manufacturing process Methods 0.000 description 3
230000007935 neutral effect Effects 0.000 description 3
108010082495 Dietary Plant Proteins Proteins 0.000 description 2
241000196324 Embryophyta Species 0.000 description 2
108090000371 Esterases Proteins 0.000 description 2
102100022624 Glucoamylase Human genes 0.000 description 2
206010060862 Prostate cancer Diseases 0.000 description 2
208000000236 Prostatic Neoplasms Diseases 0.000 description 2
239000005862 Whey Substances 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
239000006227 byproduct Substances 0.000 description 2
ZZIALNLLNHEQPJ-UHFFFAOYSA-N coumestrol Chemical compound C1=C(O)C=CC2=C1OC(=O)C1=C2OC2=CC(O)=CC=C12 ZZIALNLLNHEQPJ-UHFFFAOYSA-N 0.000 description 2
230000001419 dependent effect Effects 0.000 description 2
230000002255 enzymatic effect Effects 0.000 description 2
229940011871 estrogen Drugs 0.000 description 2
239000000262 estrogen Substances 0.000 description 2
238000012545 processing Methods 0.000 description 2
239000002195 soluble material Substances 0.000 description 2
239000002904 solvent Substances 0.000 description 2
238000012360 testing method Methods 0.000 description 2
FRAUJUKWSKMNJY-UHFFFAOYSA-N 5-hydroxy-3-(4-hydroxyphenyl)-7-(6-malonyl-beta-D-glucopyranosyloxy)-4H-1-benzopyran-4-one Natural products OC1C(O)C(O)C(COC(=O)CC(O)=O)OC1OC1=CC(O)=C2C(=O)C(C=3C=CC(O)=CC=3)=COC2=C1 FRAUJUKWSKMNJY-UHFFFAOYSA-N 0.000 description 1
TWCMVXMQHSVIOJ-UHFFFAOYSA-N Aglycone of yadanzioside D Natural products COC(=O)C12OCC34C(CC5C(=CC(O)C(O)C5(C)C3C(O)C1O)C)OC(=O)C(OC(=O)C)C24 TWCMVXMQHSVIOJ-UHFFFAOYSA-N 0.000 description 1
PLMKQQMDOMTZGG-UHFFFAOYSA-N Astrantiagenin E-methylester Natural products CC12CCC(O)C(C)(CO)C1CCC1(C)C2CC=C2C3CC(C)(C)CCC3(C(=O)OC)CCC21C PLMKQQMDOMTZGG-UHFFFAOYSA-N 0.000 description 1
241000282693 Cercopithecidae Species 0.000 description 1
102000001301 EGF receptor Human genes 0.000 description 1
108060006698 EGF receptor Proteins 0.000 description 1
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
108700041567 MDR Genes Proteins 0.000 description 1
OFOBLEOULBTSOW-UHFFFAOYSA-L Malonate Chemical compound [O-]C(=O)CC([O-])=O OFOBLEOULBTSOW-UHFFFAOYSA-L 0.000 description 1
102100024295 Maltase-glucoamylase Human genes 0.000 description 1
206010028980 Neoplasm Diseases 0.000 description 1
108010064851 Plant Proteins Proteins 0.000 description 1
108010059820 Polygalacturonase Proteins 0.000 description 1
206010036618 Premenstrual syndrome Diseases 0.000 description 1
108010073771 Soybean Proteins Proteins 0.000 description 1
238000002835 absorbance Methods 0.000 description 1
238000005903 acid hydrolysis reaction Methods 0.000 description 1
239000012445 acidic reagent Substances 0.000 description 1
108010028144 alpha-Glucosidases Proteins 0.000 description 1
239000011260 aqueous acid Substances 0.000 description 1
102000006995 beta-Glucosidase Human genes 0.000 description 1
108010047754 beta-Glucosidase Proteins 0.000 description 1
235000019658 bitter taste Nutrition 0.000 description 1
201000011510 cancer Diseases 0.000 description 1
150000001720 carbohydrates Chemical class 0.000 description 1
235000014633 carbohydrates Nutrition 0.000 description 1
231100000357 carcinogen Toxicity 0.000 description 1
239000003183 carcinogenic agent Substances 0.000 description 1
239000003518 caustics Substances 0.000 description 1
235000019506 cigar Nutrition 0.000 description 1
238000010960 commercial process Methods 0.000 description 1
238000004891 communication Methods 0.000 description 1
230000009849 deactivation Effects 0.000 description 1
238000001514 detection method Methods 0.000 description 1
238000011161 development Methods 0.000 description 1
230000018109 developmental process Effects 0.000 description 1
235000005911 diet Nutrition 0.000 description 1
230000037213 diet Effects 0.000 description 1
238000007865 diluting Methods 0.000 description 1
230000002526 effect on cardiovascular system Effects 0.000 description 1
102000015694 estrogen receptors Human genes 0.000 description 1
108010038795 estrogen receptors Proteins 0.000 description 1
108010093305 exopolygalacturonase Proteins 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
235000013305 food Nutrition 0.000 description 1
235000012041 food component Nutrition 0.000 description 1
239000005417 food ingredient Substances 0.000 description 1
230000002538 fungal effect Effects 0.000 description 1
230000008570 general process Effects 0.000 description 1
PFOARMALXZGCHY-UHFFFAOYSA-N homoegonol Natural products C1=C(OC)C(OC)=CC=C1C1=CC2=CC(CCCO)=CC(OC)=C2O1 PFOARMALXZGCHY-UHFFFAOYSA-N 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
ADFCQWZHKCXPAJ-UHFFFAOYSA-N indofine Natural products C1=CC(O)=CC=C1C1CC2=CC=C(O)C=C2OC1 ADFCQWZHKCXPAJ-UHFFFAOYSA-N 0.000 description 1
230000005764 inhibitory process Effects 0.000 description 1
150000002632 lipids Chemical class 0.000 description 1
238000004811 liquid chromatography Methods 0.000 description 1
FRAUJUKWSKMNJY-RSEYPYQYSA-N malonylgenistin Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](COC(=O)CC(O)=O)O[C@H]1OC1=CC(O)=C2C(=O)C(C=3C=CC(O)=CC=3)=COC2=C1 FRAUJUKWSKMNJY-RSEYPYQYSA-N 0.000 description 1
230000009245 menopause Effects 0.000 description 1
238000002156 mixing Methods 0.000 description 1
239000003471 mutagenic agent Substances 0.000 description 1
231100000707 mutagenic chemical Toxicity 0.000 description 1
230000011340 peptidyl-tyrosine autophosphorylation Effects 0.000 description 1
235000021118 plant-derived protein Nutrition 0.000 description 1
239000000843 powder Substances 0.000 description 1
210000002307 prostate Anatomy 0.000 description 1
238000011002 quantification Methods 0.000 description 1
230000036632 reaction speed Effects 0.000 description 1
238000011160 research Methods 0.000 description 1
QEVHRUUCFGRFIF-MDEJGZGSSA-N reserpine Chemical compound O([C@H]1[C@@H]([C@H]([C@H]2C[C@@H]3C4=C(C5=CC=C(OC)C=C5N4)CCN3C[C@H]2C1)C(=O)OC)OC)C(=O)C1=CC(OC)=C(OC)C(OC)=C1 QEVHRUUCFGRFIF-MDEJGZGSSA-N 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
238000000638 solvent extraction Methods 0.000 description 1
229940001941 soy protein Drugs 0.000 description 1
239000007921 spray Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
239000006228 supernatant Substances 0.000 description 1
208000024891 symptom Diseases 0.000 description 1
235000013311 vegetables Nutrition 0.000 description 1
238000005406 washing Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/22—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4
- C07D311/26—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3
- C07D311/40—Separation, e.g. from natural material; Purification
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/22—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4
- C07D311/26—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3
- C07D311/34—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3 with aromatic rings attached in position 3 only
- C07D311/36—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3 with aromatic rings attached in position 3 only not hydrogenated in the hetero ring, e.g. isoflavones
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H17/00—Compounds containing heterocyclic radicals directly attached to hetero atoms of saccharide radicals
- C07H17/04—Heterocyclic radicals containing only oxygen as ring hetero atoms
- C07H17/06—Benzopyran radicals
- C07H17/065—Benzo[b]pyrans
- C07H17/07—Benzo[b]pyran-4-ones

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Genetics & Genomics (AREA)
Molecular Biology (AREA)
Engineering & Computer Science (AREA)
Biochemistry (AREA)
Biotechnology (AREA)
General Health & Medical Sciences (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Preparation Of Compounds By Using Micro-Organisms (AREA)
Saccharide Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Soy Sauces And Products Related Thereto (AREA)
Beans For Foods Or Fodder (AREA)
Micro-Organisms Or Cultivation Processes Thereof (AREA)
Pyrane Compounds (AREA)

ES97304076T 1996-06-11 1997-06-11 Procesos para recuperar las isoflavonas de las mezclas de soja. Expired - Lifetime ES2247617T3 (es)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US661845		1996-06-11
US08/661,845 US5821361A (en)	1996-06-11	1996-06-11	Recovery of isoflavones from soy molasses

Publications (1)

Publication Number	Publication Date
ES2247617T3 true ES2247617T3 (es)	2006-03-01

Family

ID=24655352

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
ES97304076T Expired - Lifetime ES2247617T3 (es)	1996-06-11	1997-06-11	Procesos para recuperar las isoflavonas de las mezclas de soja.

Country Status (14)

Country	Link
US (9)	US5821361A (ja)
EP (3)	EP1659119A1 (ja)
JP (1)	JPH1067770A (ja)
KR (1)	KR100412117B1 (ja)
CN (1)	CN1195750C (ja)
AT (1)	ATE302767T1 (ja)
AU (1)	AU720462B2 (ja)
BR (1)	BR9703526A (ja)
CA (1)	CA2207360C (ja)
DE (1)	DE69734042T2 (ja)
ES (1)	ES2247617T3 (ja)
MX (1)	MX9704375A (ja)
RU (1)	RU2219785C2 (ja)
TW (1)	TW474930B (ja)

Families Citing this family (139)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP0656786B2 (en)	1992-05-19	2014-04-23	Novogen Research Pty Ltd	Use of isoflavone phyto-oestrogen extracts of soy or clover
US5821361A (en)	1996-06-11	1998-10-13	Protein Technologies International, Inc.	Recovery of isoflavones from soy molasses
US6521282B1 (en)	1996-08-09	2003-02-18	Protein Technologies International, Inc.	Aglucone isoflavone enriched vegetable flour and grit
US6579561B2 (en)	1996-08-09	2003-06-17	Protein Technologies International, Inc.	Aglucone isoflavone enriched vegetable flour and vegetable grit and process for making the same from a vegetable material containing isoflavone
AUPO203996A0 (en)	1996-08-30	1996-09-26	Novogen Research Pty Ltd	Therapeutic uses
US6146668A (en) *	1997-04-28	2000-11-14	Novogen, Inc.	Preparation of isoflavones from legumes
EP0979074A4 (en)	1997-05-01	2003-07-09	Novogen Inc	TREATMENT OR PREVENTION CLIMATE ACTION SYMPTOMS AND OSTEOPOROSIS
US8039026B1 (en)	1997-07-28	2011-10-18	Johnson & Johnson Consumer Companies, Inc	Methods for treating skin pigmentation
US6228993B1 (en)	1998-10-12	2001-05-08	Central Soya Company, Inc.	Soy isoflavone concentrate process and product
US6320028B1 (en)	1997-10-15	2001-11-20	Central Soya Company, Inc.	Soy isoflavone concentrate process and product
US6369200B2 (en)	1997-10-15	2002-04-09	Central Soya Company, Inc.	Soy isoflavone concentrate process and product
US6004558A (en) *	1998-02-25	1999-12-21	Novogen, Inc.	Methods for treating cancer with legume plant extracts
US6132795A (en) *	1998-03-15	2000-10-17	Protein Technologies International, Inc.	Vegetable protein composition containing an isoflavone depleted vegetable protein material with an isoflavone containing material
AUPP260798A0 (en)	1998-03-26	1998-04-23	Novogen Research Pty Ltd	Treatment of medical related conditions with isoflavone containing extracts of clover
US5994508A (en) *	1998-04-13	1999-11-30	Protein Technologies International, Inc.	Isoflavone rich protein isolate and process for producing
US6083553A (en) *	1998-06-05	2000-07-04	Protein Technologies International, Inc.	Recovery of isoflavones from soy molasses
US8106094B2 (en)	1998-07-06	2012-01-31	Johnson & Johnson Consumer Companies, Inc.	Compositions and methods for treating skin conditions
US6750229B2 (en)	1998-07-06	2004-06-15	Johnson & Johnson Consumer Companies, Inc.	Methods for treating skin pigmentation
US8093293B2 (en)	1998-07-06	2012-01-10	Johnson & Johnson Consumer Companies, Inc.	Methods for treating skin conditions
CN1184895C (zh) *	1998-07-16	2005-01-19	阿龙·塔博尔	大豆组合物及其促进健康的应用
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1996
- 1996-06-11 US US08/661,845 patent/US5821361A/en not_active Expired - Fee Related
1997
- 1997-06-09 CA CA002207360A patent/CA2207360C/en not_active Expired - Lifetime
- 1997-06-10 KR KR1019970023720A patent/KR100412117B1/ko not_active Expired - Fee Related
- 1997-06-10 AU AU24813/97A patent/AU720462B2/en not_active Ceased
- 1997-06-10 TW TW086107983A patent/TW474930B/zh not_active IP Right Cessation
- 1997-06-11 CN CNB97114995XA patent/CN1195750C/zh not_active Expired - Fee Related
- 1997-06-11 BR BR9703526A patent/BR9703526A/pt not_active Application Discontinuation
- 1997-06-11 RU RU97109364/13A patent/RU2219785C2/ru not_active IP Right Cessation
- 1997-06-11 ES ES97304076T patent/ES2247617T3/es not_active Expired - Lifetime
- 1997-06-11 AT AT97304076T patent/ATE302767T1/de not_active IP Right Cessation
- 1997-06-11 DE DE69734042T patent/DE69734042T2/de not_active Expired - Fee Related
- 1997-06-11 EP EP05018137A patent/EP1659119A1/en not_active Withdrawn
- 1997-06-11 EP EP05018136A patent/EP1659118A1/en not_active Withdrawn
- 1997-06-11 JP JP9153660A patent/JPH1067770A/ja active Pending
- 1997-06-11 EP EP97304076A patent/EP0812837B8/en not_active Expired - Lifetime
- 1997-06-11 MX MX9704375A patent/MX9704375A/es unknown
1998
- 1998-05-29 US US09/086,658 patent/US5919921A/en not_active Expired - Fee Related
- 1998-12-03 US US09/204,808 patent/US6323018B1/en not_active Expired - Lifetime
- 1998-12-03 US US09/204,431 patent/US5990291A/en not_active Expired - Lifetime
2001
- 2001-10-19 US US10/016,461 patent/US6495141B2/en not_active Expired - Lifetime
2002
- 2002-10-30 US US10/283,671 patent/US20030119759A1/en not_active Abandoned
- 2002-12-12 US US10/318,154 patent/US6706292B2/en not_active Expired - Lifetime
- 2002-12-13 US US10/319,730 patent/US6664382B2/en not_active Expired - Lifetime
- 2002-12-16 US US10/320,792 patent/US6680381B1/en not_active Expired - Lifetime

Also Published As

Publication number	Publication date
US6680381B1 (en)	2004-01-20
CN1174839A (zh)	1998-03-04
BR9703526A (pt)	1998-10-06
US6706292B2 (en)	2004-03-16
CN1195750C (zh)	2005-04-06
US5990291A (en)	1999-11-23
US6495141B2 (en)	2002-12-17
KR100412117B1 (ko)	2004-06-16
AU720462B2 (en)	2000-06-01
ATE302767T1 (de)	2005-09-15
KR980002040A (ko)	1998-03-30
EP1659119A1 (en)	2006-05-24
US20030118675A1 (en)	2003-06-26
DE69734042D1 (de)	2005-09-29
CA2207360A1 (en)	1997-12-11
EP0812837B8 (en)	2005-10-26
MX9704375A (es)	1998-04-30
TW474930B (en)	2002-02-01
DE69734042T2 (de)	2006-06-14
US5821361A (en)	1998-10-13
US6664382B2 (en)	2003-12-16
EP0812837B1 (en)	2005-08-24
US5919921A (en)	1999-07-06
AU2481397A (en)	1997-12-18
CA2207360C (en)	2002-08-13
RU2219785C2 (ru)	2003-12-27
US20030129263A1 (en)	2003-07-10
US20020072591A1 (en)	2002-06-13
EP1659118A1 (en)	2006-05-24
US6323018B1 (en)	2001-11-27
US20030119759A1 (en)	2003-06-26
EP0812837A1 (en)	1997-12-17
JPH1067770A (ja)	1998-03-10

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